S$ 448 Find Cheap Flights from Chicago to Singapore

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Singapore departing on 4-9. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Best Singapore Flight Deals from Chicago

Cheapest return prices found by our users on KAYAK in the last 72 hours
Singapore
Singapore1 stopS$ 868
Singapore
Singapore1 stopS$ 868

Cheap Flights from Chicago to Singapore

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights from Chicago to Singapore that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals from Chicago to Singapore

seg, 1 set - seg, 6 out
Air India Logo
12:00 - 19:30ORD-SIN
42h 30m1 stop
Air India Logo
23:00 - 07:25SIN-ORD
45h 25m1 stop
S$ 868Air India
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seg, 1 set - seg, 22 set
Air India Logo
12:00 - 19:30ORD-SIN
42h 30m1 stop
Air India Logo
23:00 - 07:25SIN-ORD
45h 25m1 stop
S$ 869Air India
Find Deal
qua, 27 ago - qua, 3 set
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
Cathay Pacific Logo
20:05 - 14:25SIN-ORD
31h 20m1 stop
S$ 886Cathay Pacific
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seg, 22 set - dom, 28 set
Cathay Pacific Logo
16:00 - 05:30ORD-SIN
24h 30m1 stop
Cathay Pacific Logo
01:50 - 14:25SIN-ORD
25h 35m1 stop
S$ 892Cathay Pacific
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ter, 9 set - qua, 19 nov
Turkish Airlines Logo
19:50 - 08:45ORD-SIN
23h 55m1 stop
Turkish Airlines Logo
23:25 - 10:05SIN-ORD
24h 40m1 stop
S$ 1,026Turkish Airlines
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qua, 5 nov - dom, 16 nov
Turkish Airlines Logo
20:20 - 08:45ORD-SIN
22h 25m1 stop
Turkish Airlines Logo
10:25 - 10:05SIN-ORD
37h 40m1 stop
S$ 1,039Turkish Airlines
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ter, 26 ago - ter, 2 set
Delta Logo
09:15 - 23:40MDW-SIN
25h 25m2 stops
Delta Logo
22:30 - 18:37SIN-MDW
33h 07m2 stops
S$ 1,466Delta
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qua, 10 set - qua, 17 set
Delta Logo
09:15 - 05:00MDW-SIN
30h 45m2 stops
Delta Logo
07:30 - 21:36SIN-MDW
27h 06m2 stops
S$ 1,468Delta
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seg, 18 ago - seg, 1 set
Korean Air Logo
09:15 - 23:40MDW-SIN
25h 25m2 stops
Korean Air Logo
01:10 - 12:28SIN-MDW
24h 18m2 stops
S$ 1,875Korean Air
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ter, 14 out - qua, 5 nov
Korean Air Logo
09:20 - 23:40MDW-SIN
25h 20m2 stops
Korean Air Logo
22:30 - 12:28SIN-MDW
27h 58m2 stops
S$ 1,903Korean Air
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Booking Insights

KAYAK's insights & trends for Chicago to Singapore flights

Get data-powered insights and trends into flights from Chicago to Singapore to help you find the cheapest flights, the best time to fly, and much more.

What is the cheapest month to fly from Chicago to Singapore?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago to Singapore is February, when tickets cost S$ 1,129 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of return tickets is S$ 2,285 and S$ 1,839 respectively.

What’s the cheapest day of the week to fly from Chicago to Singapore?

The average price of all round-trip flights from Chicago to Singapore clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Singapore, you should consider leaving on a Wednesday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

How far in advance should I book a flight from Chicago to Singapore?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to Singapore, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below-average price on a flight from Chicago to Singapore, you should book around 4 weeks before departure, which saves you about 17% compared to booking last-minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

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Good to know

Low seasonApril
Cheapest flightS$ 448
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly (53% more expensive on average)
Flight from Chicago O'Hare Airport to Singapore

FAQs - booking Singapore flights

  • How does KAYAK find such low prices on flights from Chicago to Singapore?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Singapore.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Singapore?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Singapore is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Singapore?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly from Chicago to Singapore with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Singapore?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Chicago to Singapore up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Singapore?

    The cheapest time of day to fly to Singapore is generally in the evening, when retur flights cost S$ 1,799 on average. Morning departures are around 28% more expensive than evening flights, on average. The most expensive time of day to fly to Singapore is generally in the morning, which is peak travel time and where the average cost of a ticket is S$ 2,310.

Reviews of the top airline flying from Chicago to Singapore

 
Need help choosing which airline to fly with from Chicago to Singapore? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.3
Turkish AirlinesOverall score based on 3925 reviews
7.3Comfort
7.3Boarding
7.4Entertainment
7.4Food
7.7Crew
Airline reviews

The economy seat was so uncomfortable, had not enough leg room for 13 hours flight, front seat basket was broken and couldn’t hold anything, food quality was horrible( we got food poisoned ) we charged for logged which used to be free. We paid too much for this flight and very disappointed. Turkish air line better to make satisfy and respect people instead of find different way to scam people.

4.0 OkayAnonymous, Jul 2025LAX - IST
Read more Turkish Airlines reviews

The economy seat was so uncomfortable, had not enough leg room for 13 hours flight, front seat basket was broken and couldn’t hold anything, food quality was horrible( we got food poisoned ) we charged for logged which used to be free. We paid too much for this flight and very disappointed. Turkish air line better to make satisfy and respect people instead of find different way to scam people.

This is really the rating of two flights. JFK to IST then IST to NQZ. New York to Istanbul was good. Good crew and all positives. The flight to Astana was so bad that brought it all down. Crew was nonexistent above the minimum, seats were cramped, and it was hot on the plane. Turkish Airlines seems to be slipping down to US based carriers level.

The 2 agents on the check in counter were super nice , helpful and very polite. Boarding was like a 1 2 3, I would recommend Turkish airlines for your next trip.

Everything was very good, except that the plane was an hour and a half late

flight with heavy turbulence old boeing 777 rest wasnt clean dashboard doesn’t work

Light and recline did not work on my seat. Very uncomfortable and could not read in the dark

Bad experience; they are not good anymore. They charge too much for luggage seat are so uncomfortable, Flight delays which may miss your next flight, they don’t care if you miss the flight or not. Zero customer services for front desk representatives Istanbul's airport I’m not using this airline any more.

I’ve been traveling for 20 years. I tried Turkish airline for the first time horrible horrible service and it would be my last time even if I get offer for a free ticket, I will not accept it. They have races and the worst Flight attendant

It wasn't good. I didn’t understand. They changed 320 dollars for 2 luggage. My ticket was regular and I paid almost 1200.00 dollars. Why they did charge? I want my money back.. thanks Yılmaz polat

Very punctual, the onboard staff was friendly and correct, the flight was fortunately very calm, the toilets were clean, in short, an excellent experience Thanks

Everything you need to know for your flight from Chicago to Singapore

Cabin class types available on flights to Singapore

Cabin classes available on flights to Singapore. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
First Class flights from Chicago to Singapore
Business Class flights from Chicago to Singapore
Prem Econ Class flights from Chicago to Singapore
Economy class flights from Chicago to Singapore

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